1007093-77-7Relevant academic research and scientific papers
Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids
Haley, Hannah M. S.,Payer, Stefan E.,Papidocha, Sven M.,Clemens, Simon,Nyenhuis, Jonathan,Sarpong, Richmond
supporting information, p. 4732 - 4740 (2021/04/07)
Nitrogen heterocycles (azacycles) are common structural motifs in numerous pharmaceuticals, agrochemicals, and natural products. Many powerful methods have been developed and continue to be advanced for the selective installation and modification of nitrogen heterocycles through C-H functionalization and C-C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage diversification of a readily accessible common precursor, N-desmethyl-β-obscurine. Key steps in the syntheses include oxidative C-C bond cleavage of a piperidine ring in the core structure of the obscurine intermediate and site-selective C-H borylation of a pyridine nucleus to enable cross-coupling reactions.
Enantiospecific formal total synthesis of (+)-fawcettimine
Jung, Michael E.,Chang, Jonah J.
supporting information; experimental part, p. 2962 - 2965 (2010/09/15)
The diastereospecific attack of the silyl enol ether on the activated cyclopropyl diester 27 generated the hydrindanone 28 with complete stereocontrol. Thermal decarbomethoxylation of 28 gave the monoester 29, a key intermediate in Heathcocks synthesis, thereby completing a formal total synthesis of (+)-fawcettimine 1. The analogous cyclization of 33, the diastereomer of 27, afforded the diastereomeric diester 34, thereby demonstrating that the cyclization process is diastereospecific.
Intermolecular radical addition reactions of α-iodo cycloalkenones and a synthetic study of the formal synthesis of enantiopure fawcettimine
Liu, Kuan-Miao,Chau, Chi-Min,Sha, Chin-Kang
, p. 91 - 93 (2008/09/19)
The generation of α-carbonyl vinyl radicals from α-iodo cycloalkenones, the scope of their participation in intermolecular addition reactions with electron-withdrawing olefins are studied and a synthetic study of the formal synthesis of enantiopure fawcet
